The Often Pathetic Love Life of Sam Winchester
by visionsofmangos
Summary: Sam's usually fail love life, from his first crush at age 7 through Jess. Of course, Dean does some meddling, because that's what big brothers do, right?  rated T to be on the safe side for some of Dean's commentary
1. Chapter 1

The first time Sam Winchester fell in love, he was seven years old.

Her name was Elisabeth Saunders, and she was, without a doubt, the cutest girl in his second-grade class. At first Sam had been reluctant to make any friends in this new Missouri town – he'd really liked their last house, being back in Kansas for a little while; even if he didn't remember it, that's where he was born, and he wasn't happy about having to move _again_ – but the moment he laid eyes on Elisabeth, he changed his opinion. Of course, that didn't mean he made friends instantly. Sammy Winchester was actually really nice, or at least he thought so, but he didn't make friends easily. Dad said it was probably because he was smart and shy, which put people off. Dean snorted and muttered that it was because Sammy was to smart for his own good and downright obnoxious to top it off.

Even with Elisabeth Saunders in the equation, Sam wasn't sure about the whole new friends thing. But he couldn't just walk up to the girl herself without support, so he resigned himself to making a new impression on his classmates. He started talking to Kenny Holdsworth and Jason Morgan, and after a while, he came to call them friends. They were playing video games at Kenny's house when Sam worked up the nerve to ask them about Elisabeth.

"Girls? Ick," Kenny replied, mashing a few more buttons in an attempt to fend off an oncoming horde of aliens. Sam sighed; Kenny was in the camp that clung firmly to the belief that girls had cooties and would have nothing to do with them.

"I dunno, Sammy," Jason said, stretching lazily. "I think she likes Tyler Wind." Sam struggled to remember who Tyler was, and grimaced as he pictured Tyler's spiky, gelled blonde hair, big blue eyes, and "adorable" (or so he'd heard it described) smattering of freckles across his nose. Sam, awkwardly tall for his age, with floppy hair that fell more in the "unkempt" range rather than the cute puppy look, and his general lack of people skills, was no match for Tyler in a competition for a girl's attention.

"Good choice, though," Jason congratulated him approvingly. "Lissy's pretty cute."

After more alien-smashing, Sam went home, feeling very depressed. It appeared that his first ever love campaign would be over before it began.

Dad was at work – regular work, not the supernatural-beasty-hunting kind – so Sam dejectedly sat at the kitchen counter in their tiny, two-bedroom apartment and poured himself a bowl of cereal. Morosely, he swirled the cereal around in the bowl with a spoon. He'd checked in the fridge for milk, but the bottle they had was two weeks past its sell-by date. Sam had sniffed it hopefully, but after he almost puked from the smell, he decided he was better off without it. If you can eat the milk, you shouldn't, Dean always said.

Speaking of Dean. Sammy raised his head, searching for his brother. Dad would never leave him home alone for long without Dean there to babysit him, despite the fact that Sam thought he was well capable of fending for himself by now, but he hadn't heard a peep from the bedroom they shared. "Dean?" he called.

"Mmrf," Dean replied, which Sam took to be a muffled "shut your cake hole, I'm sleeping." He didn't particularly care, though. Dean, at age eleven, had just reached his two-week anniversary with his first girlfriend, and Sammy wondered if maybe his big brother could give him tips on how to win over Elisabeth. He wasn't quite ready to give up on her yet, he realized, and Dean just might have the answers.

(It would be many years and many violently awkward situations later that Sam_ finally_ learned not to ask his brother for dating advice, but for now, he was clueless and Dean was somewhat innocent, or at least for Dean Winchester he was innocent, and so it would take a while for Sammy to discover that Dean was really not the right guy to ask for help on these occasions.)

Sam padded almost silently to their bedroom and peeked in the door. Dean lay sprawled across his bed, which was the bottom bunk (Sam still didn't understand why he, as the younger brother, was expected to sleep on top, but again, this was before he discovered lots of things about his brother, such as Dean's fear of heights – it wasn't a fear of heights, Dean always argued; it was a fear of falling, which was perfectly rational – but again, at seven, Sammy rarely thought to question his brother's motives) with a car magazine next to him. He blinked sleepily at Sam and asked, "Humnerhuf?"

"You really need to learn not to make up languages when you're sleepy," Sam admonished, only half-joking.

"Shut up, Sammy," Dean mumbled, which was really the only English phrase he could enunciate clearly in his sleep. Well, that, and something about pie.

"Dean," Sam began tentatively, "you… you really like Annie, right? Like, you_ like_ like her?"

Dean glared. "You're really not going to let me sleep, are you, kid?" he complained, but he sat up anyway. "Of course I like her, weirdo. She's my girlfriend."

"Have you kissed her?" Sam asked curiously. He didn't think he was interested in doing _that_ with Elisabeth yet, no matter how much he liked her; he found the very idea of kissing kind of gross, actually. Spit exchange? Eww. No thanks.

Dean colored. "What? No!" (Innocent still, remember. In the future, Sam would tease him mercilessly about this moment.)

Not wanting to annoy his brother before he'd even gotten to the point of the conversation Sam quickly backpedaled. "Well, I mean, it's just, you're dating, so…"

"Ugh, Sammy, just shut up!" Dean was still bright red, so he pulled a classic Dean Winchester move: he went to deflect the attention from himself. "Why? Why's it matter to you?"

"Well," Sam said hesitantly, "there… there's this girl."

Dean snorted. "Of _course _there's a girl. Jeez, I didn't think I'd have to have The Talk with a seven-year-old, but then, you always were precocious."

Sammy hurried to head off _that _discussion, having heard terrible things about The Talk from his peers in school. "No, no. I mean, she's…" He tried to think of a way to describe the girl of his dreams. "She's Elisabeth," he said finally, as if that explained everything.

Dean rolled his eyes. "Okay, so what is it exactly that you want, Sam?"

Sam blinked; he hadn't considered that far in his quest for Elisabeth Saunders' heart yet. "I… I don't know."

"Like, do you want her to be your girlfriend? Or whatever it is that little kids do when they like each other?"

Sam thought long and hard, which was how he usually thought. "I guess I just want her to like me," he said at last.

"Okay, well, first you're going to have to tell her you like _her_," Dean advised. "Otherwise this whole campaign is going nowhere."

Sam panicked. "I can't tell her that! What if she doesn't like me back? It would be super embarassing!"

"Aw, Sam, don't shoot down your chances before you've even started. Let's just start with talking to her, alright?" Dean smirked at him. "Have you even said two words to her since we moved here?"

"Of course," Sam said defensively. When Dean raised an eyebrow, he admitted, "Well… one. I said thanks once when she held the door for me."

"Now there, Sammy boy, is your first mistake. You gotta hold the door for the lady, not let her hold it for you." Dean shook his head in clear disappointment. "Guess the whole gentleman manners thing got lost somewhere in between rock salt guns and summoning rituals, huh?"

"So what do I do?" Sam begged desperately.

Dean ruffled his little brother's hair affectionately. "Let's start by saying hello."


	2. Chapter 2

The second time Sam Winchester fell in love, it was with a sexy, well-endowed, shiny-spandex-wearing superhero in one of Dean's comic books, but after the whole "you-can't-bang-fictional-characters-so-stop-drooling-into-your-broccoli-son" debacle (John Winchester did not have time for any distractions, no matter how pretty, while he was training his boys or out on a hunt), he wouldn't even acknowledge the incident. He didn't fall in love again until high school. Sure, there were crushes here and there, but Sam refused to let it develop any further. The longest they'd ever lived in one place was seven and a half months, and that didn't exactly lend itself to significant relationships.

But even the most rational human being has to give in to his heart at some point.

He was fifteen – almost old enough to drop out, as Dean often reminded him – and the Winchesters had just relocated to a small town in rural Tennessee. Dean at least was happy. He got a kick out of the southern accents, and he took full advantage of his longish sandy hair and bright green eyes every chance he got. He had a new girl every week or so, which drove Sam crazy, but since when had Dean ever listened to sense?

Sam liked to think he was a little more mature, but the day Abigail Wilson wore that white dress to school, he lost all sense of superiority and gave in to the long-suppressed hormonal side of his brain. Abigail was short, but not too short, much like her dress – it rose above the knee, which was near scandalous in a backwoods town like this, but it wasn't like it showed half her thigh or anything, and the neckline was conservative enough. She was cute, but also smart – she was in Sam's honors English class and advanced biology – and she drove most of the boys in school crazy with her unflappable charm. When she passed Sam in the hall, sashaying her tiny hips in that white dress, Sam's mouth fell open and he outright stared. The dress accentuated her subtle curves, and her long dark hair flowed in loose curls down her back, not restrained in its usual braid.

Sam was reduced to a gaping, speechless idiot.

He eventually regained his senses, although he was late to Spanish. "Dude," he said breathlessly to Eric, his best friend in this town. "Abigail Wilson…" He trailed off, noticing the _profesora_ was giving him and Eric the evil eye.

Eric grinned. "_Buena suerte, amigo_," he smirked. "Good luck with that. She's a feisty little thing. Plus—"

"_¡Chicos!_" bellowed Sra. Green. "_No hables en ingles en mi clase, por favor._"

Appropriately chastised, Sam immediately shut up.

To his surprise, Dean was in the kitchen when he got home. "Dude. Aren't you supposed to be at work?" Sam asked.

Dean responded with his usual snark. "Dude. Aren't you supposed to be in school?"

Sam opened the refrigerator door in a vain effort to find an unspoiled jug of milk. "Shut up. You know school's over."

"Yeah, like, an hour ago. What'd you do, stay after for chess club?"

"Math tutoring," Sam mumbled, mouth full of very stale pretzels.

"Tutoring?" Dean looked genuinely surprised. "What happened, Sammy?"

"No, I mean, I was the one doing the tutoring. Some kid needed help in trig, which I happen to remember really well from last year, so I stayed after to help him," Sam explained. "Anyway, why aren't you at work?"

Dean shrugged. "Boss kicked me out. Weren't enough cars to work on, so he figured he'd give me a half day."

"Huh. Well, bonus for you, then."

The brothers were silent for a bit. Dean was the one to break it, obviously "What's on your mind, Samantha? You got girly troubles or somethin'?"

"Call me Samantha one more time," Sam threatened, "and I will tell Dad what you were_ really_ doing during that job last week when you said you had work."

"Hey, that Darlene chick was hot!" Dean shot back. "Besides, that's not the point. You've got something goin' on in that big brain of yours, Sam. Spill."

Sam heaved a huge, overly dramatic sigh, just to irritate his brother. "Well, there's a girl."

"Of course there's a girl. So who is she?"

"Abigail Wilson."

Dean whistled through his teeth. "You sure know how to pick 'em, don't you?"

"What do you mean?"

"Her dad comes into the shop sometimes. He's a real piece of work. Crazy protective of his daughter, too. And she's got three older brothers."

"Oh, man." Sam cradled his head in his arms. "How am I going to…"

"Start small. Just talk to her," Dean advised. Clearly he understood that this situation was too serious for his usual ribbing. After all, it had been a long time since he'd had an opportunity to meddle with Sam's life like this.

"We already talk; she sits in front on me in English."

Dean gave him a lecherous grin. "Checking her out from the best angle, huh?"

Sam gritted his teeth. "They were assigned seats."

"Uh huh. At least you got the first part right."

Sam stared at his brother for a moment in confusion, and then blushed when he figured out what Dean meant. "It's not like that! Not all of us are such… such_ pervs_, Dean." Sam shuddered. "I just want to ask her out on a date. One date."

Dean rolled his eyes. "Innocent little Sammy. But, fine. You want to ask her out, go ahead. I'll do my best to keep Pa Wilson from beating on you."

Sam began rambling. "So where should we go? What do I wear? What if she doesn't even like me like that?"

"First, I didn't hear a _thank you_. I just promised to keep some overprotective dad away from you, and I don't even get a measly _thanks_? Jeez, Sam, don't come running to me when some old guy shoves a shotgun in your face because he thinks you deflowered his little girl. Second, you're worrying about what to _wear_? Seriously? How gay are you?"

"Dean, I am currently attempting to win the favor of someone who's quite obviously female. Is my sexuality really in question here?"

"Whoa there, buddy. Knock it off with the big words."

"Alright, Dean, I'll make sure to keep it to two or three syllables, just for you," Sam snarked. "But seriously, what do you do for a first date?"

"Here's a tip for ya, Sam – don't get too far ahead of yourself. You gotta do the asking bit first, then start worrying your pretty head about the details."

Too late for that advice; Sam was already anxious. "I have to at least have an idea of what we're going to do! All the magazines say to ask her on a specific date, so if she turns you down –"

"Really, Samantha, must you rely on chick magazines for your dating info? With your big brother right here? I'm offended."

"Because you're so much help," Sam muttered.

"Okay, okay. How about this: ask her to a movie on Friday, and if she says yes – which she will, mind; no female can resist the Winchester charm—" Sam snorted. "—and if she doesn't suggest a particular movie, I'll help you come up with one. Sound good?"

Sam didn't really see how he could argue that point, so he agreed and ran off to consider possible outfits for the big day.


End file.
